Winn was born on June 9, 1895, in New London, Missouri. Until 1930, he operated a candy store.[2]
A Democrat, Winn was elected clerk of Ralls County in 1930, serving as such until being elected State Treasurer of Missouri in November 1936. He served as Treasurer between January 1937 and 1941, and earned $3,000 annually. During his tenure, the Treasury received the responsibilities of the Missouri State Social Security Commission. From 1941 to January 1945, he was commissioner of the Permanent Seat of Government, after which he served his second, nonconsecutive tenure, between January 1945 and his death. For his second tenure, he earned $7,500 annually.[2][3] Ten days prior to his death, he won the Democratic primary for Missouri Secretary of State.[4] He could sing, which he did during his political campaigns.[3] Also for campaigns, he used the slogan "Win With Winn" and appealed to working people.[5]
On December 7, 1921, Winn married Victoria Silver; they had one daughter together. He died in office on August 13, 1948, aged 53. He had been hospitalized the day prior, due to coronary thrombosis, dying in St. Luke's Hospital, in St. Charles. His funeral was held in Jefferson City,[6] and he is buried in New London.[4][5] After his death, Richard R. Nacy was appointed by Governor Phil M. Donnelly to filled his unexpired term, himself also serving a consesucutive term.[2][3]
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